The development of synthetic routes which lead to five new diisocyanide monomers with one or two phenolic groups is described. Their polymerization behavior is studied with Pd- and Ni-based initiators, as well as under microwave irradiation. The polymerizability is mainly dominated by steric effects as is concluded from experiments using different protecting groups. Chiroptical properties of these new polymers are studied by CD-spectroscopy. After deprotection, helically chiral poly(quinoxalin-2,3-diyl)s are obtained which display a BrOnsted function attached to a stereolabile biaryl axis whose configuration should be influenced by the chiral polymer backbone. (c) 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 1320-1329